WO2012149091A2 - Compositions d'élastomères durcissables ayant une capacité d'étanchéité à basse température - Google Patents

Compositions d'élastomères durcissables ayant une capacité d'étanchéité à basse température Download PDF

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Publication number
WO2012149091A2
WO2012149091A2 PCT/US2012/035094 US2012035094W WO2012149091A2 WO 2012149091 A2 WO2012149091 A2 WO 2012149091A2 US 2012035094 W US2012035094 W US 2012035094W WO 2012149091 A2 WO2012149091 A2 WO 2012149091A2
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Prior art keywords
composition
cured
oligomer
sealing
elastomeric
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Ceased
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PCT/US2012/035094
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WO2012149091A3 (fr
Inventor
Matthew P. Burdzy
Dingsong Feng
Kevin J. WELCH
Yanbing Wang
Robert P. Cross
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Henkel Corp
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Henkel Corp
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Priority to EP12777777.9A priority Critical patent/EP2702112B1/fr
Priority to JP2014508535A priority patent/JP2014517857A/ja
Priority to CN201280020474.1A priority patent/CN103492504B/zh
Priority to KR1020137027910A priority patent/KR102092287B1/ko
Priority to ES12777777T priority patent/ES2808700T3/es
Publication of WO2012149091A2 publication Critical patent/WO2012149091A2/fr
Publication of WO2012149091A3 publication Critical patent/WO2012149091A3/fr
Priority to US13/796,588 priority patent/US20130287980A1/en
Anticipated expiration legal-status Critical
Priority to US14/682,251 priority patent/US10005919B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/04—Homopolymers or copolymers of esters
    • C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09D133/08—Homopolymers or copolymers of acrylic acid esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B37/1284—Application of adhesive
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
    • C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
    • C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C08L23/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C08L23/22—Copolymers of isobutene; Butyl rubber; Homopolymers or copolymers of other iso-olefins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C09D123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C09D123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
    • C09J123/02—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers not modified by chemical after-treatment
    • C09J123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C09J123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • C09J123/22—Copolymers of isobutene; Butyl rubber ; Homo- or copolymers of other iso-olefines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
    • F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
    • F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
    • F16J—PISTONS; CYLINDERS; SEALINGS
    • F16J15/00—Sealings
    • F16J15/02—Sealings between relatively-stationary surfaces
    • F16J15/14—Sealings between relatively-stationary surfaces by means of granular or plastic material, or fluid
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2003/1034—Materials or components characterised by specific properties
    • C09K2003/1068—Crosslinkable materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0617—Polyalkenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
    • C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
    • C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09K2200/0625—Polyacrylic esters or derivatives thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/13—Hollow or container type article [e.g., tube, vase, etc.]
    • Y10T428/1352—Polymer or resin containing [i.e., natural or synthetic]

Definitions

  • the present disclosure relates generally to curable sealant compositions having low temperature sealing ability Improved over convention curable sealing compositions.
  • Sealants are used in a broad range of applications from automobiles to aircraft engines to contain or prevent solids, liquids, and/or gases from moving across a mating surface, boundary or interfacia! region Into or on a surrounding or adjacent area, reg on or surface. Sealants are available in many forms from low viscosity liquids to highly thlxotropic pastes and depending on the application can vary in properties from a rigid glassy material to a rubbery elastic network. Elastomers are an important class of polymeric materials useful as sealing compositions and the focus of the current invention.
  • curing compositions ingredients thai react to form new covending bonds that increase the molecular weight of the chemical backbone leading to entanglements and/or chemical cross-links that exhibits elastic properties are generally referred to as "curing" compositions.
  • Curing Sealants containing ingredients that do not react but exhibit elastic properties based on the thermodynamic properties of the polymer, entanglement of network chains or other molecular interactions are generally referred to as “non-curing" formulations,
  • the equation of state for rubber elasticity describes the relationship between macroscopic sample deformation of a polymer (chain extension) and the retractive stress of the elastomer.
  • the theory of rubber elasticity derived from the second la of thermodynamics, states that the retractive stress of an elastomer arises as a result of the reduction in entropy upon extension and not changes in enthalpy. As a polymer chain is extended the number of conformations decrease (entropy decreases) and the retractive stress increases. Sperling writes that a long-chain molecule, capable of reasonably free- rotation about Its backbone joined together in a continuous network Is required for rubber elasticity.
  • ⁇ is the stress
  • n is the number of active network chains per unit volume
  • R is the ideal gas constant
  • T is temperature
  • the equation of state predicts that as the extension of an elastomer increases the observed stress increases.
  • the stress Is the retractiv force created when for example an elastomer is placed under tension, biaxial tension or compression.
  • the utility of an elastomeric sealant is measured by the ability of the cured sealant composition to provide a positive sealing force when exposed to operating conditions over the lifetime of the product. Temperature is an important factor that affects the performance of a sealant and can have a significant impact on the operating lifetime. The temperature range in harsh ambient conditions can vary from ⁇ r15G to ⁇ 85X. In less severe applications temperatures can vary from -M00 to ⁇ 40°C.
  • the composition is flovvable and can be cured to a cross linked form to provide cured reaction products that exhibit elastomeric properties.
  • the curable elastomeric sealant composition can include a cross linkable elastomeric oligomer; an initiator or cross-linking agent: a glassy monomer and/or a rubbery monomer; and optionally one or more of a catalyst: a filler; an antioxidant; and an optional reaction modifier.
  • the cross linkable eiastomehc sealant composition can be prepared by reacting a cross linkable elastornerie oligomer having a.
  • Tg with at least one of a glassy monomer and a rubbery monomer.
  • Cured reaction products of the composition have a single Tg and retain a higher sealing force at low temperatures (but abov the cured product Tg) as compared to a curable composition made from the same cross linkable elasiomenc oligomer but without the glassy and/or rubbery monomer,
  • the cross linkable- efastonwic oligomer s a telechelic polyisobuiyfene (FIB) based material terminated at each end with acrylate moieties.
  • Another aspect provides a component having a first predetermined sealing surface aligned with a second predetermined sealing surface.
  • a cured reaction product of a polyisofoutylene (PIS) based composition is disposed between the sealing surfaces to prevent movement of materials such as liquids, gasses or fuels between the aligned sealing surfaces.
  • the composition may be cured in contact with one, both or none of the sealing surfaces.
  • the seal formed by the cured reaction product provides low temperature sealing (about -40°C) within the rubbery region along with excellent resistance to moisture, water, glycols, adds, bases and polar compounds,
  • the disclosed compounds include any and all isomers and stereoisomers.
  • the disclosed materials and processes may be alternately formulated to comprise, consist of, or consist essentially of, any appropriate components, moieties or steps herein disclosed.
  • the disclosed material and processes may additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any components, materials, ingredients, adjuvants,, moieties, species and steps used In the prio art compositions or that are otherwise not necessary to the achievement of the function and/or objective of the present disclosure,
  • FIG. 1 is a relaxation recovery sequence for the cured materia! of example 3.
  • the lower plot is temperature at the time shown and the uppe plot is sealing force of that, cured material at the time shown,
  • FIG. 2 Is a scan from the Differential Scanning Calorimeter analysis of the cured products of composition of Example 1
  • FIG. 3 is a scan from the Differential Scanning Calorimeter analysis of the cured products of composition of Example 2.
  • FIG. 4 is a scan from the Differential Scanning Calorimeter analysis of the cured products of composition of Example 3.
  • FIG. 5 is a scan from the Differentia! Scanning Calorimeter analysis of the cured products of composition of Example 24.
  • FIG. 8 is a scan from the Differential Scanning: Calorimeter analysis of th cured
  • FIG. 7 is a scan from the Differential Scanning Calorimeter analysis of the cured products of composition of Example 34.
  • FIG, 8 is a graph showing sealing force at ⁇ 40°C for compositions of Examples 1 ⁇ 2 and 3 having varying oligomer : monomer ratio.
  • a curable elasion ic sealant composition is a composition that is flo able and can he cured to a cross linked form to provide cured reaction products of the composition that
  • the curable elastomerlc sealant composition can include a cross linkable aiastomeric oligomer-; an initiator or cross-linking agent; a glassy monomer and/or a rubbery monomer; and optionally one or more of a catalyst; a filler; an antioxidant; and an optional reaction modifier.
  • the cross linkable elastomerlc sealant composition can be prepared by reacting a cross linkable elastomerlc oligomer having a T ⁇ with at least one of a glassy monomer and a rubbery monomer.
  • the cross linkable eiastomerio sealant composition can be cured by exposure to conditions and for a time sufficient to at least partially cross-link and cure that composition.
  • Suitable cure conditions, depending on formulation of the cross linkable elastomerlc sealant composition include exposure to heat and radiation such as actinic radiation,
  • Cured reaction products of the composition have a single Tg as measured by Differential Scanning Calorimetry (DSC) and retain a higher sealing force at low temperatures (hut above the cured product Tg) as compared to a curable composition made from the same cross linkable eiastomerio oligomer but without the glassy and/or rubbery monomer.
  • sealant chemistries are believed to be suitable for use in the sealant composition.
  • These chemist ies include fly oe!astomer; EPDM and other hydrocarbons; styrenic block elastomer; CA and C3 ⁇ 4 monomers such as isoprene and isobutyiene; acrylates and methaery!ates; acrylic emulsion; ethylene acryfate elastomer; functional ted polyacryiate; silylated acryiate; silicone; silylated poiyether; silylated polyester; silylated po!yamide; polyurethane; silylated polyurethane; plasilsol and polyvinyl chloride; polysuifide and poiyihioether; flexible epoxy; vinyl acetate ⁇ ethylene latex; unsaturated polyester; polyo!efins, amides and acetates for example EVA, Non-curable chemistries such as
  • the curable elastomerlc sealant composition advantageously Includes a cross linkable elastomerlc oligomer.
  • 8 oligomer is a tetechelic, polyisobutylene polyme with acrylate moieties- at each end (pplyisobutylen ⁇ diacrylate or PI8 diacrylate). glass monome
  • the curable elasfomeric sealant composition can include a glassy monomer that is reacted with the cross linkable elastomerie oligomer, A glassy monome has a glass transition temperature above the glass transition temperature of the cross linkable elasfomeric oligomer. Typically the glassy monomer has a glass transition temperature above 2G C 'C.
  • glassy monomers include staary! acrylate (Tg 3S°C); thme!hyleyclohexyl methacrylate (Tg 145°C); isobornyl methacrylate (Tg 110°C); isobornyl acrylate (Tg 88 e C); and the FANCRYL meihacry) esters marketed by Hitachi Chemical Corporation such as dlcyelopentanylmeth crylate (FA-5 ZM Tg 175°C) and dlcyclopentanyl Acrylate (FA-513AS, Tg 140 i5 C).
  • FANCRYL meihacry FANCRYL meihacry
  • the curable elastomeric sealant composition can include a rubbery monomer that i reacted with the cross linkable elasfomeric oligomer, A rubbery monomer has a glass transition temperature below the glass transition temperature of the glassy monomer. Typically the rubbery monomer has a glass transition temperatur below 20°C.
  • Rubbery monomers include isooctyi acrylate ⁇ Tg --54° € ⁇ ; isodecyl acrylate (Tg ⁇ 60°C); isodecyl methacrylate (Tg ⁇ 41°C): n-lauryl methacrylate (Tg -85); and 1 ,12-dodecanediol dimethacryiafe (Tg ⁇ 37 if C), Other examples of glassy and rubbery monomers are listed In the Tables at the end of the specification.
  • the curable elasfomeric sealant composition can include an initiator or cross-linking agent to at least partially cross-link and cure that composition.
  • the initiator or cross-linking agent can foe a heat-cure initiator or initiator system comprising an ingredient or a combination of ingredients which at the desired elevated temperature conditions produce free radicals
  • Suitable initiators may Include peroxy materials, e t., peroxides, hydroperoxides, and peresfers. which under appropriate elevated temperature conditions decompos to form peroxy free radicals which are Inifiatlncjly effective for the polymerization of the curable elaslomerie sealant compositions.
  • the peroxy materials may be employed in concentrations effective to initiate curing of the curable elastomeric sealant composition at a desired temperature and typically In concentrations of about 0,1% to about 10% by weight of composition.
  • Another useful class of heat-curing initiators comprises azonitnle compounds which yield free radicals when decomposed by heat. Heat is applied to the curable composition and the resulting free radicals initiate polymerization of the curable composition.
  • Azonitnte Initiators of the above-described formula are readily commercially available, the initiators which are commercially available under the trademark VAZO from E, I, DuPont de Nemours and Company, Inc., Wilmington, D£,
  • Photolnitiators enhance the rapidity of the curing process when the photocura ' bie elastorrieric sealant composition is exposed to electromagnetic radiation, suc as actinic radiation, for example ultraviolet (UV) radiation.
  • electromagnetic radiation suc as actinic radiation
  • UV radiation ultraviolet
  • Some useful photolnitiators include, but are not limited to, photolnitiators available commerciall from Clba Specialty Chemicals, under the iRGACURE” and “DAROCUR” trade names, specifically "IRGACtlRE” 184 (1 -hyciroxycyclohexy!
  • photoinitiatefs useful herein include alkyl pyruvates, such as methyl, ethyl, propyl and buiyl pyruvates, and aryl pyruvates, such as phenyl, benzyl, and
  • Photoinitiators particularly well-suited for use herein include ultraviolet photoinitiators, such as 2,2 «dsmetho.xy-2-phenyf aeetophenone ⁇ e.g., "IRGACURE” 851), and 2-hydroxy-2 ⁇ methyl-1 ⁇ phenyM -propane (e.g., "DARDCUR M 1173), bis(2,4 ( 8 fimefhy! benzoyl) phenyl phosphine oxide (e.g., "IRGACURE” 819), and the ultraviolet/visible photoinitiaior combination of bi&(2,6 ⁇ diniethoxybenzo 1-2 i 4 !
  • the actinic radiation used to cure the photocurable elastomehc sealant composition has a wavelength from about 200 nm to about 1 ,000 nm.
  • Useful UV includes, but is not limited to, UVA (about 32.0 nm to about 410 nm), UVB (about 290 nm to about 320 nm), UVC (about 220 nm to about 290 nm) and combinations thereof.
  • Useful visible light includes, but is not limited to, blue light, green light, and combinations thereof.
  • Photoinitiators can he employed in concentrations effective to initiate curing of the curable elasiomene sealant composition at a desired exposure to actinic radiation and typically In concentrations of about 0.01% to about 10% by weight of composition.
  • the ' Durable elastomeric sealant composition can include a catalyst ' to modify speed of the initiated reaction. filler
  • the curable elastomeric sealant composition can optionally include a filler.
  • a filler include, for example, tithopone, zirconium silicate, hydroxides, such as hydroxides of calcium, aluminum, magnesium, iron and the like, dlatomaceous earth, carbonates, such as sodium, potassium, calcium, and magnesium carbonates, oxides, such as zinc, magnesium, chromic, cerium, zirconium and aluminum oxides, calcium clay, fumed silicas, silicas that have been surface treated with a silane or sllazane such as the AEROSIL products available from Evonik Industries, silicas that have been surface treated with an acrylate or methacryiafe such as AEROSIL 7200 or R711 available from Evonik Industries, precipitated silicas, untreated silicas, graphite, synthetic fibers and mixtures thereof.
  • filler can be employed in concentrations effective to provide de-sired physical properties in the uncured composition and cured
  • the curable elastomeric sealant composition can optionally include an anti-oxidant
  • Some useful antioxidants include those available commercially from Ciba Specialty Chemicals under the tradename IRGANOX. When used, the antioxidant should be used in the range of about 0.1 to about 16 weight percent of curable composition, such a about 0.3 to about 1 weight percent of curable composition. reaction modifier.
  • the curable elastomeric sealant composition can include a reaction modifier.
  • a reaction modifier is a material that will increase or decrease reaction rate of the curable elastomeric sealant composition.
  • quinones such as hydroquinone, monomethyl ether hydroquinone ⁇ IVIEHQ ⁇ , nap h thoquinone and anthraqulnone, may also be included to scavenge free radicals in the curable eiastorneric sealant composition and thereby slow reaction of that composition and extend shelf life.
  • the reaction modifier can he used in the range of about 0.1 to about 15 weight percent of curable composition. adhesion promoter,
  • the curable e!astomehc sealant composition can include one or more adhesion promoters that are compatible and known in the art.
  • adhesion promoters include octyl fnmethoxysi!ane ⁇ commercially available from Chamtura under the trade designation A-137), giycidyl tnmethoxysilane (commercially available from Chemtura under the trade designation A--187). methacryfoxypropyl trimeihoxysliane (commercially available from Chemiura under the trade designation of A- 174). vinyl frimethoxysilane, tetraethoxysiiane and its partial condensation products, and combinations thereof.
  • the adhesion promoter can be used In the range of about 0.1 to about 16 weight percent of curable composition. rheology modifiers,
  • the curable eiastorneric sealant composition can optionally include a thlxofropic agent to modify rheological properties of the uncured composition.
  • thixotropic agents include, for example, silicas, such as fused or fumed silicas, that may he untreated or treated so as to alter the chemical nature of their surface. Virtually any reinforcing fused, precipitated silica, fumed silica or surface treated silica may be used, [46] Examples of treated fumed silicas include polydimethylsiloxane-treaied silicas, hexamethy!disi!azane-treated silicas and other silazane or sllane treated silicas.
  • Such treated silicas are commercially available, such as from Cabot Corporation under the tradename CAB-O-SIL D-TS and Evonik Industries under the tradename AERGS!L, such as AEROSIL R8Q5. Also useful are the silicas that have been surface treated with an acrylate or methacryiate such as AEROSIL R7200 or 711 available from Evonik Industries. [46j Examples of untreated silicas include commercially available amorphous silicas ' such as AEROSIL 380, AE OSIt 200 and AEROSIL 130. Commercially available hydrous silicas include IPSIt El 50 and IPSIL E20QA manufactured by Japan Silica Kogya Inc.
  • rheology modifier can be employed m concentrations effective to provide desired physical properties in the uncured composition and cured reaction products and typically In concentrations of about 0.1% to about 70% by weight of composition. coloring agent.
  • the curable elastorne-ric composition can be dear to translucent
  • a colored composition can be beneficial to allow for Inspection of the applied composition.
  • a coloring agent for example a pigment or dye, can be used to provide a desired color beneficial to the Intended application.
  • Exemplar coloring agents include titanium dioxide, C.I. Pigment Blue 28, G.I. Pigment Yellow 53 and phthaiocyanine blue EN.
  • a fluorescent dye can be added to allow inspection of the applied composition under UV radiation.
  • Th coloring agent will be present in amounts sufficient to allow for detection, if present, the coloring agent is desirably Incorporated in amounts of about 0.002% or more by weight The maximum amount is governed by considerations of cost and absorption of radiation that interferes with cure of the composition. Mo desirably, the dye is present in amounts, of about 0.002% to about 1.0% weight by weight of the total composition.
  • the curable elastomeric sealant composition can optionally include other additives at concentrations effective to provide desired properties so long as they do not inhibit the desirable properties such as curing mechanism, elongation, low temperature sealing force, tensile strength, chemical resistance.
  • additives include, for example, reinforcing materials such as fibers, diluents, reactive diluents, coloring agents and pigments, moisture scavengers such as rnethylbimethoxysilane and vinyltrimethylo ysifane, inhibitors and the like may be Included.
  • Exemplary composition ange :
  • a curable eiastomeric sealant composition can typically comprise:
  • reaction modifier about 0 to 15 wt % of a reaction modifier
  • adhesion promoter about 0 to 15 wt% of adhesion promoter
  • the glassy rnonomer(s) and the rubbery monomer(s) can be chosen so that a desired average glass transition temperature for that combination of monomers is obtained.
  • the average glass transition temperature for a combination of monomers is defined by the Fox equation (1/Tg 0 on* ⁇ * see T.G. Fox, Bull. Am. Phys,
  • the ratio of cross linkable eiastomeric- oligomer to glassy monomer must be chosen to provide sufficient glassy monomer to increase low temperature sealing force of the cured sealant reaction products. However, the ratio must not add so much glassy monomer that the eiastomeric properties of the cored sealant reaction products are undesirably affected. Thus, there is a need to balance the ratio of cross linkable eiastomeric oligomer to glassy monomer depending on desired properties: too little glassy material and the cured sealant composition will not have a desirable low temperature sealing force but too much glassy material and sealing ability of the cured sealant at higher temperatures is lost
  • the ratio of cross linkable eiastomeric oligomer to glassy monomer will depend on the oligomer and monomer used; the final application for the sealant; and the cured sealant properties desired for that application.
  • a ratio of cross linkable eiastorrserle oligomer to glassy monomer In the range of 75 : 25 to 96 : 5 respectively provides a general starting point. At present there is no way to predict cured sealant properties for a cross linkable sealant composition formulation. Testing of formulations for low temperature sealing force and higher temperature sealing properties is required to arrive at a formulation and ratio providing desired properties,
  • sealant composition viscosity can be formulated for application method and desired cycle time
  • Viscosity of the uncured sealant composition can be 10,000 Cps to 1 ,000,000 Cps at 25 0.
  • Specific physical properties required for cured reaction products of the sealant composition will depend on sealing application, minimum: and maximum operating temperatures within the application, desired tensile strength at high temperatures and desired sealing force at low temperatures.
  • Some useful physical properties for the cured reaction products include: Hardness, Shore A about 20 to about 90 and desirably about 40 to about 60, Tensile strength, about 100 psi to about 2,000 psi and desirably about 500 psi to about 1 ,000 psi. Elongation, about 10% to about 1 ,000% and desirably about 100% to about 500%, Low temperature ⁇ -40 a C) sealing force, about 0 Newtons to about SO Newtons and desirably about 6 Newtons to about 30 Newtons.
  • the cured reaction product has a compression set value that allows a seal made therefrom to maintain a predetermined minimum sealing force throughout the design life of the seal
  • [SO] Components to be sealed by the disclosed curable compositions have a first predetermined sealing surface that is aligned with a second predetermined sealing surface.
  • the aligned sealing surfaces are in a fixed relationship and move very little relative to each other.
  • the aligned sealing surfaces are generally In fluid communication with a chamber. The seal formed between the aligned sealing surfaces prevents movement of materials between the surfaces and Into, or cut of, the chamber.
  • One or both of the sealing surfaces can be machined or formed.
  • predetermined sealing surfaces are designed to allow a curable composition to be disposed on one or both surfaces daring initi assembly of the component to form a seal therebetween Design of the predetermined sealing surfaces enhances
  • a predetermined sealing surface does not encompass surfaces that were not identified or designed prior to initial assembly to accommodate a seal or gasket, for example the outside surface of a component over which a repair material is molded or applied to lessen leaking.
  • Sealing surfaces on an engine block and oil pan or engine intake manifold are examples of sealing surfaces in fixed
  • the disclosed curable compositions can be in a flowable state for disposition onto at least a portion of one sealing surface to form a seal between the surfaces when they are aligned.
  • the curable composition can be applied as a film over the sealing • surface.
  • the curable composition can also be applied as a bead in precise patterns by tracing, screen printing, robotic application and the like, in bead applications the disclosed compositions are typically dispensed as a liquid or semi-solid under pressure through a nozzle and onto the component sealing surface.
  • the nozzle size Is chosen to provide a line or bead of composition having a desired width, height, shape and volume.
  • the curable composition can foe contained in a small tube and dispensed by squeezing the tube: contained in a cartridge and dispensed by longitudinal movement of a cartridge sealing member; or contained in a larger container such as a 5 gallon pall or ⁇ 55 gallon drum and dispensed at the point of use by conventional automated
  • Container size can be chosen to suit the end use application.
  • the curable composition can be used to form a formed in place gasket (FIPG).
  • FIPG formed in place gasket
  • the composition is dispensed onto a first predetermined sealing surface.
  • the first predetermined sealing surface and dispensed composition is aligned and seailngly engaged with a second predetermined sealing surface before the
  • the curable composition has fully cured.
  • the composition will adhere to both sealing surfaces as It cures.
  • the curable composition can be used to form a cured in place gasket (C!PG).
  • C!PG cured in place gasket
  • the composition Is dispensed onto a first predetermined sealing surface and allowed to substantially cure before contact with a second predetermined sealing surface.
  • the first sealing surface and cured composition is sealmgty engaged with the second sealing surface thereby compressing the cured composition to provide a seal between the sealing surfaces.
  • the composition will adhere to only the first sealing surface.
  • the curable composition can be used to form a moid in place gasket (jVl G),
  • the part comprising the first predetermined sealing surface is placed in a moid.
  • the composition is dispensed into the mold where it contacts the first sealing surface.
  • the composition is typically allowed to cure before removal from the moid.
  • the first sealing surface and molded composition is seallngi engaged wit a second predetermined sealing surface thereby compressing the cured
  • composition to provide a seal between the sealing surfaces.
  • the composition will adhere to only the first sealing surface.
  • the curable composition can be used in liquid Injection molding (L!IVI).
  • L!IVI liquid Injection molding
  • uncured composition is dispensed into a mold without any predetermined sealing surface under controlled " pressure and temperature.
  • the composition is typically allowed to cure before removal from the mold. Alter removal the molded part, will retain its shape.
  • the molded gasket Is disposed between two predetermined sealing surfaces and compressed to provide a seal between the sealing surfaces.
  • PI8 diacryiate is a telechellc, poiyisobutyiene polymer with acryla e moieties at each end , with a molecular weight of about 1 ,000 to about 1 ,000,000 and a very low glass transition temperature (Tg) of ⁇ 67 a C.
  • Tg glass transition temperature
  • PIB diacryiate was chosen as the rubber matrix of the elastomerio gasketlng compositions, PIB diacryiate can be prepared using a number of known reactions schemes, some of which are listed below and the contents of which are incorporated by reference herein in their entirety. The method of scheme 2 can be used to prepare the PIB diacryiate .used in the following compositions:
  • Premix preparation Charge all liquids including initiator, antioxidant, reaction
  • Gompression set 8 (%, 25%) 62 41 27 7 11
  • Compression set B values of greater than 0 but less than 40 Indicate a cured material may have an advantageous lowlomperatUm sealing force.
  • the high compression set B value (62) of Example 1 indicates a cured material that will not maintain desirable sealing force at low temperatures.
  • Example 43 is a UV curable composition.
  • Example 43 was formed into samples. The samples were exposed to an UV ⁇ radiation source having an intensity of about 1434 mw/cm for an energy of about 9872 mJ cm 2 . Cured samples of composition 43 had a sealing force at -4Q°C of at 26% compression.
  • Example 44 is a thermally curable composition,
  • the sealing force fo example 24 is shown in the fable below as a function of temperature and percent compression.
  • the composition in example 24 exhibits typical e!astornerlc properties.
  • the sealing force at a constant temperature Increases as the percent compression is increased, which is expected based on the theory of rubber elasticity as the extension increases.
  • the force, al a constant compression Increases as the temperature is increased. This is also expected based on the temperature dependency defined in the equation of state of rubber elasticity.
  • a high viscosity Is undesirable as it is difficult to rapidly dispense th composition.
  • a lo elongation is undesirable which can lead to cracks in the seal
  • a high sealing force at low temperature is desirable as this defines the practical lower limit of ability of the elastorneric seal to perform its intended function over the operating temperature range.
  • the low temperature sealing force i.e. at -40°C, can be modulated dramatically with changes in the glassy and/or rubbery monomer ratio.
  • Each of these cured networks exhibited a single glass transition temperature when measured with a differential scanning caiorimeir (DSC) as shown in Figures 2, 3 and 4 (Examples 1 , 24 and 30).
  • DSC differential scanning caiorimeir

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Abstract

L'invention concerne des compositions d'étanchéité durcissables ayant une capacité d'étanchéité à basse température, améliorée par rapport à des compositions d'étanchéité durcissables classiques. La composition est apte à s'écoulemer et peut être durcie en une forme réticulée pour fournir des produits de réaction durcis qui présentent des propriétés élastomères. La composition d'étanchéité élastomère durcissable peut comprendre un oligomère élastomère réticulable ; un amorceur ou un agent de réticulation ; un monomère vitreux et/ou un monomère caoutchouteux ; et éventuellement, un ou plusieurs parmi un catalyseur ; une charge ; un agent colorant ; un anti-oxydant ; et un modificateur de réaction facultatif. La composition d'étanchéité élastomère réticulable peut être préparée par réaction d'un oligomère élastomère réticulable ayant une Tg avec au moins l'un parmi un monomère vitreux et un monomère caoutchouteux. Les produits de réaction durcis de la composition possèdent une seule Tg et conservent une force d'étanchéité supérieure aux basses températures (mais au-dessus de la Tg du produit durci) par comparaison avec une composition durcissable produite du même oligomère élastomère réticulable mais sans le monomère vitreux et/ou caoutchouteux.
PCT/US2012/035094 2011-04-27 2012-04-26 Compositions d'élastomères durcissables ayant une capacité d'étanchéité à basse température Ceased WO2012149091A2 (fr)

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EP12777777.9A EP2702112B1 (fr) 2011-04-27 2012-04-26 Compositions d'élastomères durcissables ayant une capacité d'étanchéité à basse température
JP2014508535A JP2014517857A (ja) 2011-04-27 2012-04-26 低温シーリング機能を備える硬化性エラストマー組成物
CN201280020474.1A CN103492504B (zh) 2011-04-27 2012-04-26 具有低温密封能力的可固化的弹性体组合物
KR1020137027910A KR102092287B1 (ko) 2011-04-27 2012-04-26 저온 밀봉 성능을 갖는 경화성 엘라스토머 조성물
ES12777777T ES2808700T3 (es) 2011-04-27 2012-04-26 Composiciones de elastómeros curables con capacidad de sellado a baja temperatura
US13/796,588 US20130287980A1 (en) 2011-04-27 2013-03-12 Curable elastomer compositions with low temperature sealing capability
US14/682,251 US10005919B2 (en) 2011-04-27 2015-04-09 Curable elastomer compositions with low temperature sealing capability

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US201161479710P 2011-04-27 2011-04-27
US61/479,710 2011-04-27

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US13/796,588 Continuation US20130287980A1 (en) 2011-04-27 2013-03-12 Curable elastomer compositions with low temperature sealing capability
US14/682,251 Continuation US10005919B2 (en) 2011-04-27 2015-04-09 Curable elastomer compositions with low temperature sealing capability

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US20130287980A1 (en) 2013-10-31
KR20140045929A (ko) 2014-04-17
US10005919B2 (en) 2018-06-26
EP2702112A2 (fr) 2014-03-05
TW201302996A (zh) 2013-01-16
JP2014517857A (ja) 2014-07-24
KR102092287B1 (ko) 2020-03-23
JP6473186B2 (ja) 2019-02-20
CN103492504B (zh) 2017-06-23
WO2012149091A3 (fr) 2013-01-17
JP2017206675A (ja) 2017-11-24
US20150210882A1 (en) 2015-07-30
EP2702112A4 (fr) 2015-01-21
EP2702112B1 (fr) 2020-05-13
CN103492504A (zh) 2014-01-01
ES2808700T3 (es) 2021-03-01

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